Divot

Derek Andersen
  • 5.0 (18)
  • BUSINESS
  • UPDATED WEEKLY

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

  1. #30: How Gusto’s CEO Built a Category-Defining Company - Leadership, Scaling & Long-Term Growth

    3D AGO

    #30: How Gusto’s CEO Built a Category-Defining Company - Leadership, Scaling & Long-Term Growth

    Josh Reeves, co-founder and CEO of Gusto, shares how he built one of the most trusted platforms for small businesses, and what it truly takes to scale a company with purpose. In this episode, Josh breaks down the realities of building and leading a high-growth startup, navigating regulation, designing products for long-term impact, and maintaining culture as teams and responsibilities scale. He explains how focusing on customers, discipline, and long-term thinking has shaped Gusto’s journey and why sustainable growth matters more than chasing short-term wins. This conversation is a deep dive into founder mindset, leadership, and building enduring companies, essential listening for entrepreneurs, operators, and anyone serious about building something that lasts. Follow Josh - X (Twitter): https://x.com/joshuareevesFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:01:44 – Why Most Startups Fail Before They Even Begin02:27 – The Hidden Cost of Regulation03:48 – Why Payroll and Benefits Matter More Than You Think05:39 – The Real Reason Running a Business Feels So Hard07:44 – The Benefit That Completely Changed Employee Loyalty09:31 – What Sustainable Growth Actually Looks Like11:34 – The Three Metrics That Truly Matter in Business13:58 – Why Chasing Hypergrowth Can Destroy Great Companies15:48 – Building a Company Meant to Last for Decades17:20 – The Leadership Mindset That Separates Great Founders18:54 – Why Being “Busy” Is Not the Same as Making Progress20:21 – How to Identify People Who Will Actually Succeed22:46 – How AI Is Changing the Way Teams Work24:06 – Why Helping Others Is the Ultimate Advantage25:32 – The Life Lessons That Shape Great Leaders27:20 – Gratitude, Perspective, and Staying Grounded29:33 – What Success Really Means (And What It Doesn’t)31:43 – The One Principle That Guides Every Decision33:22 – A Simple Philosophy for a Meaningful Life Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork

    36 min
  2. #29: Survival, Courage & Storytelling - Fire, War & The Brother Who Never Walks Away

    12/17/2025

    #29: Survival, Courage & Storytelling - Fire, War & The Brother Who Never Walks Away

    Before he became an award-winning filmmaker and humanitarian, Brandt Andersen built a tech company from scratch, scaled it to tens of millions in revenue, and sold it before moving into filmmaking, where he went on to produce major films like Everest, Lone Survivor, and American Made. But behind the success is a life shaped by extremes: a skydiving accident that nearly killed him, surviving the Malibu fires with his son, and years spent inside war zones helping people in crisis. In this conversation, Brandt shares the real stories behind I Was a Stranger, his new film inspired by the Syrian refugee crisis. He explains how meeting smugglers, soldiers, parents, and children across Syria, Turkey, Jordan, and Haiti reshaped his understanding of judgment, fear, and humanity. This episode is also deeply personal. Brandt is Derek's older brother. Together, they revisit the moments that forged their bond: childhood chaos, life-or-death situations, and the lessons Brandt passed down through the way he lives. Their conversation reveals the heart, flaws, courage, and philosophy of a man who has spent his life running toward the fire for others, and the profound impact that has had on Derek. Learn More About Brandt - Wikipedia: https://en.wikipedia.org/wiki/Brandt_AndersenFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:1:39 — Who Brandt Andersen Really Is & Why His Story Matters3:03 — The Skydive That Should Have Killed Him8:47 — What Facing Death Taught Brandt About Life14:02 — The Wild Childhood Stories That Shaped Him18:10 — The Banksy Above His Fireplace & His Dark/Light Identity22:30 — From Startup Exit to Hollywood Storytelling28:41 — Producing Everest, Lone Survivor & American Made32:12 — The Real Families Who Inspired I Was a Stranger36:55 — Inside Syria: Crisis Through Human Eyes41:38 — “Don't Judge People by Their Worst Day”45:52 — Haiti Earthquake: Chaos, Hunger & Purpose52:10 — The Moment That Changed His View of Humanity1:12:03 — Trapped in the Malibu Fires With His Son1:29:45 — What Brandt Ultimately Wants People to Understand Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#BrandtAndersen #IWasAStranger #Filmmaking #Storytelling #SyrianRefugeeCrisis #HumanitarianAid #WarZones #Resilience #Courage #PurposeDrivenLife #LoneSurvivor #Everest #AmericanMade #Leadership #PersonalGrowth #DivotPodcast

    1h 32m
  3. #28: Reinvention & Resilience - Faith, Failure & Becoming Who You Are Meant to Be

    12/10/2025

    #28: Reinvention & Resilience - Faith, Failure & Becoming Who You Are Meant to Be

    Before he became chairman of the Napoleon Hill Institute, David Meltzer lived a life driven by scarcity, ambition, and the need to prove himself. Raised by a single mother in Akron, he chased success to change their future, eventually becoming a multimillionaire and CEO in the sports world. But behind the achievements was an identity built on ego, bad habits, and external validation, leading to the breaking point that forced him to confront who he’d become. In this conversation, David shares the mindset shift that saved his marriage, the four values that rebuilt his identity, and how losing over $100M became the foundation for a healthier, more purposeful life. He explains how faith, gratitude, sleep discipline, and time mastery helped him recover, along with the frameworks he teaches today to serve his mission of empowering over a billion people. From stop-drop-and-roll to emotional chemistry and using failure as fuel, David breaks down the tools that rebuilt his life from the inside out. A vulnerable and practical look at reinvention, this episode reveals what it truly takes to grow through loss and rebuild meaning. If you’re navigating change, recovering from setbacks, or redefining success, David’s story offers perspective, resilience, and a blueprint for living with intention. Follow David - X (Twitter): https://x.com/davidmeltzerFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:0:00 — David’s Life: The Fall That Saved Him2:21 — Akron Roots: Scarcity, Survival & a Single Mom Who Never Quit4:58 — The Dream Life That Almost Destroyed Him7:06 — His Wife’s Warning: The Sentence That Changed Everything8:44 — Rebuilding the Man: The Four Values That Brought Him Back10:51 — Losing $100M: The Collapse He Was Finally Prepared For13:02 — The Habits That Saved His Marriage, Mind & Future17:47 — Failing Faster: Why Losing Is the Only Way to Win22:06 — Emotional Alchemy: Training His Reactions Every Single Day29:32 — “Stop, Drop & Roll”: The Method That Resets His Entire Life34:39 — Ego, Pain & Perspective: Understanding the Chemistry of a Breakdown42:18 — Turning Trauma Into Purpose: How He Rewrote His Story53:17 — The One Lesson He Wants to Leave Humanity55:38 — “What I Hope God Says to Me When I Arrive” Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#DavidMeltzer #Reinvention #Resilience #Mindset #LifeLessons #PersonalGrowth #SelfImprovement #OvercomingFailure #EmotionalIntelligence #SpiritualGrowth #Leadership #DivotPodcast

    57 min
  4. #27: The Art of Photography, Vision, Rejection & Timeless Storytelling

    12/03/2025

    #27: The Art of Photography, Vision, Rejection & Timeless Storytelling

    Before becoming the photographer trusted by the world’s biggest icons, Squint built his path on discipline, creativity, and a lifelong commitment to mastering storytelling. Raised in Palo Alto and shaped by years inside a TV studio before he turned 18, he grew from a kid with a camera into a filmmaker and cinematographer behind iconic portraits of Nas, Michael B. Jordan, Dave Chappelle, Draymond Green, and Steph Curry. As co-creator of the New York Times bestselling book Shot Ready, his black-and-white, emotionally driven style reflects a belief that great photography comes from patience, intention, and truly seeing people. In this conversation, he breaks down the ingredients of a powerful photograph, motion, eyes, framing, intimacy, and explains why rejection became his greatest superpower. He shares how he wrote a list of dream subjects at age 12 and photographed every name on it, how fatherhood reshaped his purpose, and why staying in the Bay Area defined his career more than any move to LA or New York. Squint reflects on rediscovering black-and-white photography after losing his father and earning Steph Curry’s trust through consistency, humility, and discipline. A grounded masterclass in photography, vision, resilience, and legacy, showing what it takes to create work that endures. This episode is a reminder that great art is built on love, discipline, and showing up, especially when the world tells you no. Follow Squint - Instagram: https://www.instagram.com/iamsquintFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:0:00 Introduction & how Squint became a visual storyteller3:48 First camera at age five5:17 Running a TV studio at eight6:44 Deciding at ten to do this forever8:09 The list he wrote at age 129:46 Shooting Nas for the first time12:12 How he processes rejection13:46 The Killers story16:30 Identity vs his work18:47 What makes a great picture20:31 Reading emotion through the eyes22:37 Atmosphere vs the subject26:13 Black and white vs color28:41 Training his eye32:59 Mastering relationships in the industry35:32 Showing people how he sees them48:53 Steph Curry’s discipline & ego50:20 Losing his father & rebuilding56:01 What makes a great dad Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#PhotographyMasterclass #VisualStorytelling #BlackAndWhitePhotography #CinematicPortraits #ShotReady #StephCurry #CreativeDiscipline #IconicImages #ArtOfSeeing #LegacyAndPurpose #CreatorsJourney

    1 hr
  5. #26: How Great Founders Win - Global Insight, Humility & Long-Term Thinking

    11/26/2025

    #26: How Great Founders Win - Global Insight, Humility & Long-Term Thinking

    Before helping elevate the rise of global entrepreneurship, Christine Tsai, CEO & Founding Partner of 500 Global, built her path on curiosity, consistency, and an instinct for spotting potential early. From her beginnings in tech to guiding an investing platform that now reaches founders across dozens of countries, her journey reflects a belief that great companies can start anywhere, and that humility, resilience, and long-term thinking still define the world's strongest leaders. In this conversation, she breaks down the traits she's seen across exceptional founders, the realities of building companies through cycles, and how early-stage investing has evolved over the last decade. She shares lessons on ownership, clarity, adaptability, and speed, and why the most enduring teams evolve faster than the markets around them. Christine reflects on backing thousands of founders worldwide, what she looks for in leaders under pressure, and how a global perspective shapes better decisions and more intentional company building. A grounded masterclass in global insight, founder psychology, and building with purpose, offering a rare perspective on what it takes to scale, endure, and create lasting impact in a rapidly shifting world. Follow Christine - X (Twitter): https://x.com/christine_tsaiFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:0:00 — Early Curiosity, Identity & Finding Her Path3:12 — Lessons From Google & YouTube's Early Days6:58 — The Decision to Build a Global Investing Platform10:45 — Launching 500 & the Chaos of the First Years14:40 — How Early-Stage Investing Changed Over a Decade18:26 — The Traits She Sees in Exceptional Founders22:51 — Speed, Humility & the Signals That Truly Matter26:33 — Surviving Cycles & Leading Through Volatility30:55 — What Backing 3,000+ Founders Teaches You35:18 — Global Perspective: Why Innovation Comes From Everywhere39:07 — Leadership Moments That Define a CEO43:50 — Legacy, Purpose & Why Relationships Are the Real Scorecard Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#GlobalFounders #VentureCapital #StartupLeadership #EarlyStageInvesting #FounderMindset #ScalingStartups #GlobalInnovation #WomenInVC #LeadershipLessons #BuildingEnduringCompanies #Entrepreneurship #500Global

    53 min
  6. #25: How Great Leaders Think - Integrity, Impact & Making Things Happen

    11/19/2025

    #25: How Great Leaders Think - Integrity, Impact & Making Things Happen

    Before helping lead the transformation of Salt Lake City’s urban core, Mike Maughan’s journey was shaped by discipline, faith, service, and a belief that leadership is defined by integrity above everything else. In this conversation, he shares how he built his career across organizations with massive community impact, from Qualtrics to Smith Entertainment Group, and the lessons behind navigating billion-dollar city projects, activating live experiences, and helping bring an NHL team to Utah. He breaks down the principles that great leaders use to build trust, make clear decisions, and “never get blocked,” even in environments filled with complexity. He reflects on the power of in-person connection in the age of AI, the importance of working with good people, and why ego and humility must coexist for leaders to scale. From frameworks for choosing what matters to the truth about toxic cultures, he explains why solving meaningful problems creates better careers than chasing passion. A grounded masterclass in clarity, purpose, and impact, proving that real leadership is built on service, courage, and the commitment to make things happen. Follow Mike - X (Twitter): https://twitter.com/MikeMaughanFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:0:00 — Why Being Different Beats Being 10x Better1:25 — Transforming Salt Lake City’s Urban Core5:26 — The Value of In-Person Connection in the AI Era8:42 — A Framework for Choosing What Actually Matters10:02 — Working With Good People & Recognizing Integrity14:15 — The Cost of Toxic Environments19:03 — Don’t Chase Passion — Solve Big Problems25:05 — Ego + Humility: The Rare Leadership Combo31:01 — Building Five for the Fight & Meaningful Causes36:23 — Service as a Competitive Advantage43:36 — How Great Leaders Deliver Hard News57:44 — Bringing an NHL Team to Utah & Making Vision Real Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#Leadership #PurposeDriven #ScalingImpact #CommunityBuilding #HighPerformance #AIandHumanConnection #SportsBusiness #FoundersMindset

    1h 9m
  7. #24: From Detroit to Silicon Valley: Faith, Grit & Leading With Purpose in Tech & Venture

    11/12/2025

    #24: From Detroit to Silicon Valley: Faith, Grit & Leading With Purpose in Tech & Venture

    Before leading global teams and raising more than $170 million to back exceptional founders, this journey started in a crowded home on the West Side of Detroit filled with Motown, discipline, and faith. In this conversation, she shares how she went from Detroit public schools to Cass Tech and Wharton, then entered Silicon Valley and scaled teams from 14 to more than 1,000 at Google. From global leadership assignments to becoming a first-time CEO, she breaks down the lessons behind leading with conviction, humility, and principle. She reflects on navigating high-stakes decisions, building trust at the executive level, and helping guide a major strategic transaction with one of the world’s most iconic companies. From serving on public company boards to investing at the Series A and B stage, she explains how operating experience shapes venture judgment and why she built a fund designed to support underestimated talent at scale. A masterclass in purpose-driven leadership, discipline, and belief, proving that success does not require sacrificing values, family, or faith, and that building with integrity is not a weakness, but a competitive advantage. Follow Stacy - X (Twitter): https://x.com/sbp04Follow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:0:00 — Growing Up in Detroit: Faith, Family & Strong Women2:18 — Motown Culture, Community & Early Joy4:01 — Hard Things Young: Grit & Gratitude in Scarcity5:47 — “God Will Make a Way”: Faith in Difficult Moments6:58 — Two Things Can Be True: Effort vs Surrender8:32 — Education as Escape: Earning a Shot at Cass Tech10:12 — Wharton Dreams Without a Roadmap12:45 — Breaking Into Tech & Entering Silicon Valley16:22 — From 14 to 1,000 Employees: Learning to Lead at Scale19:06 — Leading in India: Humility, Culture & Listening22:54 — Becoming CEO: Pressure, Confidence & Faith28:30 — The IKEA Deal: Inside a Transformational Acquisition33:44 — How Great Boards Really Work (No Surprises Rule)48:10 — Building Cherry Rock Capital & Investing With Purpose50:20 — How She Chooses Founders & Helps Them Scale1:11:26 — Mind Over Matter: Overcoming Hard Seasons1:12:12 — Marriage Strength & Building a Life Together1:12:42 — Legacy: Faith, Kids, Meaning & Life’s Real Scorecard Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#Leadership #SiliconValley #WomenInTech #TaskRabbit #Google #VentureCapital #FaithInBusiness #Entrepreneurship #FounderMindset #ScalingStartups

    1h 14m
  8. #23: The Box Story: Startup Lessons, AI Disruption, and the Future of Work

    11/05/2025

    #23: The Box Story: Startup Lessons, AI Disruption, and the Future of Work

    Before the cloud powered the modern enterprise, it started with a college dorm, a borrowed garage, and a vision to make work simpler. In this conversation, Aaron Levie, co-founder and CEO of Box, shares how he turned a college project into a billion-dollar SaaS company. From building during the early days of the internet to leading through massive technological shifts, Aaron reveals the lessons behind Box’s evolution from a storage startup to a global platform used by 70% of the Fortune 500. He reflects on the rise of AI, how it’s reshaping the software industry, and why this moment mirrors the early days of cloud computing. From the changing economics of software to the new era of AI agents, Aaron explains what it takes to stay relevant and keep innovating when the rules of business change overnight. A masterclass in resilience, adaptability, and leadership from one of Silicon Valley’s most curious minds, proving that innovation is less about technology and more about the people who dare to rethink it. Follow Aaron - X (Twitter): https://x.com/levie Follow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps: 0:00 – Welcome to Divot: Making Your Mark on the World 0:19 – From College Project to $4 Billion Company 1:31 – Free Rent, Big Dreams & Dropping Out 2:43 – The Birth of Box and the Cloud Idea 3:49 – The Pivot That Changed Everything 6:45 – AI Disruption: Startups vs Incumbents 10:56 – The New Economics of AI and Software 13:07 – What Clay Christensen Still Teaches Us 15:31 – AI Agents and the Future of Work 20:17 – Managing Teams in the AI Era 26:10 – How Box Shifted to an AI-First Company 40:41 – Leadership, Abundance Mindset & Life Lessons Follow Divot: YouTube: https://www.youtube.com/@Divotpod X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #AI #FutureOfWork #Leadership #Startups #Entrepreneurship #SaaS #CloudComputing #AIInnovation #AaronLevie #Box #TechLeadership #DivotPodcast

    44 min
See All (31)

5
out of 5
18 Ratings

About

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

Information

  • Creator
    Derek Andersen
  • Years Active
    2K
  • Episodes
    31
  • Rating
    Clean
  • Copyright
    © Derek Andersen
  • Show Website
    Divot

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